Iodine → N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide

HRID 1615713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615713
[C:1]([N:4]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)(=[O:3])[CH3:2].[I:19](O)(=O)=O.II>C(O)C>[C:1]([N:4]1[C:8]([NH:9][C:10](=[O:12])[CH3:11])=[C:7]([I:19])[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 807IodineHCID 24345Iodic acidHCID 86717295N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamide

Produkt 1

HCID 86717296N-(2-acetyl-4-iodo-5-phenyl-pyrazol-3-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of N-(2-acetyl-5-phenyl-pyrazol-3-yl)acetamide (25.1 g, 0.103 mol), iodic acid (4.5 g, 0.026 mol) and iodine (15.7 g, 0.062 mol) in ethanol (250 mL) was heated at 50° C. for 3 h and cooled to room temperature. The reaction mixture was concentrated in vacuo and partitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution. The layers were separated and the organic washed with brine, dried (phase separator cartridge), and concentrated in vacuo to provide a mixture of the title compound and starting material (2.2:1, 30.3 g). The mixture was put in reaction again using iodic acid (1.6 g, 9.6 mmol) and iodine (9.7 g, 38 mmol) in ethanol (250 mL) under the same conditions, to provide the title compound as a solid (31.9 g).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between CH2Cl2 and 2 M Na2S2O3 aq. solution
  4. customThe layers were separated
  5. washthe organic washed with brine
  6. customdried (phase separator cartridge)
  7. concentrationconcentrated in vacuo
  8. customto provide

Quellen und Nachweise

ORD-Eintrag
ord-ddf429445601449d87da5997f6d36dde
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765762B2

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